Synthesis and cyclization of 1-arylalk-1-ene-3,5-diynylamines |
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Authors: | V. N. Sorokoumov S. N. Morozkina I. A. Balova |
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Affiliation: | (1) Chemical Faculty, Saint Petersburg State University, Saint Petersburg, 198504, Russia |
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Abstract: | An investigation of the reaction of 1-lithio-1,3-diynes, generated in situ, with nitriles has been carried out. In the case of aromatic nitriles 1-arylalk-1-ene-3,5-diynylamines are formed, which undergo dimerization and cyclization on isolation, giving 3-(alka-1,3-diynyl)-4-(alk-2-ynyl)-2,6-diarylpyridines. The effect of the nature of the substituent in the benzonitrile molecule on the selectivity of the reaction and the yield of the products has been determined. A scheme is proposed for the conversions and the structures of the intermediates have been established. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 701–710, May, 2006. |
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Keywords: | 3-(alka-1,3-diynyl)-4-(alk-2-ynyl)-2,6-diarylpyridines lithium 2-aminoethylamide 1-arylalk-1-en-3,5-diynylamines diacetylenes 1-lithio-1,3-diynes nitriles prototropic isomerization |
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